When John F. Kennedy was assassinated in 1963, the country experienced a collective sense of grief that it had not known since the death of Abraham Lincoln. Many Americans found it hard to cope with the sudden loss of this youthful, energetic president whose speeches had inspired citizens to achieve high ideals. In his shortened tenure as president, Kennedy proposed landmark civil-rights legislation, created the Peace Corps, and promoted the goal of landing on the moon. In foreign policy, his administration peacefully resolved a dramatic stand-off with the Soviet Union over the presence of missiles in Cuba, and he oversaw the buildup of the American presence in Vietnam.

Elaine de Kooning, known for her gestural portraits, held several informal sessions with him in Palm Beach, Florida, in December 1962 and January 1963. The artist was so moved by the president during these sittings that she went on to create dozens of drawings and paintings of him over the next ten months.